Table of Contents

Why go to Tuscany?
When to Go
What to Bring
What to Eat
Where to Stay
How to Get Around
Things to Do and See in Tuscany
Wine Tasting

Why go to Tuscany?

There are a multitude of reasons that you should hop on a plane bound for Florence. To begin with the obvious, Tuscany is known for producing some of the best wine in the world and you can easily plan an entire trip centered on wine tasting given how many lovely vineyards you have to choose from as well, many of which are quite close to quaint hillside towns. From chiantis to brunellos to montepulcianos, those who enjoy a glass of red wine will delight in a trip to this region. Beyond the wine, the food in this region is outstanding and the countryside, which is responsible for producing incredible wine and food, is also breath-taking. On that note, if you have ever considered a biking trip, this is one of the best places to explore by bike, although it is rather hilly so be prepared! And just cling tight to the notion that what goes up, must come down. But in my opinion you will be well rewarded for your efforts so I’d encourage you to consider some bike exploration if that interests you. On a bike or by car, it is also worth exploring one or several of the numerous small hillside towns since this is a great way to get a less touristy Tuscany experience and maybe even have the chance to converse with some locals over a glass of wine or an espresso, depending on where your wandering leads you.

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There are also many larger cities and towns around which to anchor your trip. Florence, the capital of Tuscany, is one of the most popular destinations in Italy, so it is well worth either starting or ending there, especially since it has the largest airport in the region. Even if you only have a day or two, you can see many of the most famous works of Renaissance art, cross the famous Ponte Vecchio, explore the Duomo and still have time to find a great pizzeria and eat an entire pizza since the city itself is quite compact. Beyond Florence, the cities of Pisa, Siena, Lucca and San Gemignano are all worth a stop if you are in the region.

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When to Go

Tuscany is located in the central part of Italy and has a moderate Mediterranean climate. If you’re hoping to avoid rain, then you might want to steer clear of October and November trips, but since the region does get a fair amount of rain, it’s likely that you’ll encounter some unless you go during the summer. The tradeoff you face with going in the summer is that it can get very warm and humid with temperatures in the 80’s or even low 90’s. Did I mention the humidity? As someone who is not a fan of humidity, I find it tough to travel to Italy in the summer especially since there are few places that have A/C, restaurants and hotels included. You also battle the most crowds in the summertime given that Europeans take long holidays in July and August. Personally, I love a long day of walking around and exploring different towns or cities, so I tend to enjoy Tuscany the most in late Spring (April or May). Since it’s less rainy than most places in Europe in the springtime and the weather is already in the 60’s or 70’s, this is an ideal time for me to travel to Tuscany. But that doesn’t coincide with a lot of the wine-related activities so that is something to consider if wine and getting to see the wine-making process in action is your priority.

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What to Bring

A lot of your packing will be dependent upon what type of Tuscany vacation you are planning. If you are sticking to mainly larger cities, then make sure you prioritize good walking shoes as well as layers so you can adapt to being inside and outside throughout the course of the day. For women, don’t forget that if you are going into churches, you might need to have your shoulders covered. Even in the heat of summer, you’ll need a scarf or shawl at the very least. Especially in Florence, there are many churches worth seeing, so you don’t want to be limited by wearing a tank top or sleeveless shirt. Some buildings, especially ones made of stone, also stay cool even in the heat, so you might even want an extra layer to stay comfortable.

If you are planning on doing any biking, make sure that you have appropriate attire. Depending on if you are planning a trip through a bike tour company or if you decide to try and rent bikes on your own and explore, you’ll need to bring the appropriate footwear, clothes and possibly your helmet.

In terms of suitcases, one of my least favorite things is wheeling a suitcase over cobblestones. It’s incredibly noisy so I feel as though I’m making a huge ruckus but it also gives me the impression I’m wearing out the wheels on my suitcase at an alarming rate. Cobblestones seem to be the paving material of choice in Tuscany, so it’s a fair assumption that you’ll encounter them at some point. Combined with the number of times I’ve been confronted with more than two flights of stairs and no elevator in a hotel or airbnb, I tend to opt for a backpacking backpack when I travel. They’re just much easier to carry, fit more easily in strange spaces on trains, and are generally more versatile. The one caveat is that if you are planning to bring home a bottle or two of wine in your suitcase, the soft sides of a backpacking backpack don’t provide much cushioning for your chianti classico.

What to Eat

It’s a tough call, at least for me, to say if I enjoy the gelato or the pasta more in Tuscany. I find it difficult, but I try to limit myself to one gelato a day. That being said, I can certainly remember many days that included an afternoon and an evening gelato. Switching up between fruit flavors such as raspberry or mango and richer stracciacelli, nocciolo or pistachio gives me the impression that it isn’t as decadent and I can also attest that the warmer it gets, the more likely I am to search out gelato as a way to escape from the heat. So I suppose it’s fair to say that weather directly impacts which type of food I can’t seem to get enough of. While I’ve had both outstanding gelato and so-so gelato, I don’t think I’ve ever had bad gelato, and if there is a crowd outside a particular shop, that’s usually a fairly solid indicator that you’ve found a gelateria worth trying out.

In terms of traditional Tuscan dishes, ribollita is one of the most well-known. A soup made from leftover bread and minestrone, it is quite hearty but delicious. If you are in the region during truffle season, which is November and December, then a duck ragu with white truffles will likely be a meal that you don’t soon forget, or you could opt for pasta featuring mushrooms and truffles, one of my favorite combinations. Make sure that you try at least several kinds of pecorino cheese during your travels since this is the most well-known cheese produced in the region, although ricotta made in this region is also worth seeking out. Most meals in Italy involve many courses and it is often surprising to tourists when they realize that the pasta course is often not the main course, but comes before the fish or the meat course. Many of the most popular dishes are stews, soups and otherwise heavier dishes, so if you are in the region in the warmer months, these might be less appealing. Instead, you might opt for fettunta, which is the Florentine name for bruschetta, or panzanella, a summer bread salad with tomatoes, cucumbers, onions and other seasonal vegetables dressed with oil and vinegar. One of my favorite lighter meals involves a beautifully arranged platter of prosciutto and mozzarella, especially if you are planning on a heavier dinner of one of the aforementioned specialties.

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I also would argue that you can never make a wrong pizza decision in Italy regardless of where pizza originated or which cities or regions claim to have the best or most authentic Italian pizza. Unless, of course, you decide to share a pizza. That is never the right decision. On my first trips to Italy I made the mistake of suggesting, on the first night of my stay, to my italian friend that we split a pizza at her favorite pizzeria. She looked at me with such bewilderment I thought there must have been a translation issue. But no, she was just baffled that I would even consider not eating all of the pizza myself. I’ve never made that mistake again. I almost made another classic error when the pizza arrived and I started to cut it into slices to pick up with my hands before realizing that my friend was eating hers with a knife and fork. I’ve since then seen some italians eat their pizza in a more traditional “American” fashion where they pick it up, or at least the crust, but I’m still rather wary...

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Wine making and olive oil go hand in hand, so I’m certain you will also find some incredible olive oil during your time in Tuscany. You can buy spice mixes in many of the indoor and outdoor markets that can be found in every Tuscan city, which make great gifts and also can be mixed with olive oil for a delicious bread dipping experience that also makes a great picnic lunch. The markets also have a wide variety of fruits and vegetables, many of them local, if you are looking for an inexpensive meal. Plus, ducking into a market will give you an opportunity to talk to the local vendors. Even if you don’t speak italian, gestures, especially in Italy, can go a long way toward successful communication!

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If you are looking for a sweet to accompany your espresso or cappuccino, then you can’t miss the opportunity to try biscotti. There are many types of biscotti and cookies that are unique to the region, more than I can describe here, so I’d just recommend pointing to whichever one looks best. However, I can admit to being partial to pistachio croissants. While I try to sample many of the regional specialties when I am traveling, I tend to come back to a pistachio croissant and a cappuccino as my go to breakfast by the third or fourth day. Also, be aware that in cafes, there are different prices depending on if you are taking your sweets to go or planning to enjoy an espresso while seated at one of the tables. You need to make the decision before you order. I’ve also had some experiences where you order your coffee at one part of the bar and then your food at another part, just try and observe what the italians around you are doing and you’ll be able to figure it out.

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Where to Stay

One interesting accomodation found in Italy that is worth looking into is called an agriturismo. While these can vary from quite simple and rustic to a farmhouse that feels akin to a luxury resort, the idea is that an agriturismo allows tourists to stay on an italian farm and get a sense of what life is like for those who are living and working there. They are most similar to bed & breakfasts but often will offer dinners as well as breakfasts, likely made with ingredients produced on the farm. Some even go so far as to let you participate in the work being done on the farm. This could be your chance to milk a cow or harvest grapes if that is something on your bucket list. Especially if you are hoping to explore areas outside of the cities, I would encourage you to explore this option since it will offer a more unique experience than a hotel and will likely be much less expensive as well.

If you’re interested in a more traditional lodging experience, then there are many nice airbnb options in the cities, although there will likely be fewer choices in the smaller towns. If you prefer to stay a night or two in the smaller towns, I would recommend trying to find a small boutique hotel or B&B so that you can get recommendations for dinners, wineries and other places not to be missed. While many of the larger European chain hotels can be found in cities, I wouldn’t recommend them over smaller, more unique lodging options. Given that Italy is relatively inexpensive compared to many other European countries, with a little bit of searching you will likely be able to find a good deal on a nice three star hotel in most places.

How to Get Around

As I mentioned, Florence is a great place to fly into. Or you could fly into one of the larger airports in Italy such as Rome or Milan and then take a train to Florence. The train system in Italy is generally quite reliable and easy to use for tourists, but does require some getting used to. The rumor is that the farther south you go, the less likely the trains are to be on time. I’ve had very positive train experiences in Tuscany. If you’re only planning on traveling between the larger cities, then you likely do not need to rent a car. On the other hand, if you’d like the flexibility of exploring smaller towns or are planning to cover a lot of ground in the region then a rental car is a good idea. There are many tour operators that will do half or full day tours of different areas. These are often combined with guided walking tours in one or more of the towns or cities on the itinerary so that is another option for how to explore the region and learn more about the history of the places you are visiting. Some tour operators will even do a combination of tours by bike and van so that might be a good compromise if you like the idea of doing some bike exploration but are not sure you want to commit to several days or being on your own while biking.

Things to Do and See in Tuscany

Florence is known as one of the best places in the world for Renaissance art and therefore worth a couple of days in your itinerary. To begin your foray into Renaissance art, I’d recommend starting at the Uffizi Gallery and planning on spending at least a half of a day there, if not longer. But that also depends on your appetite for art and for crowds. There are timed entry tickets available for advance purchase and that will certainly help mitigate the fatigue that you might feel if you have to wait in a long line just to get into the gallery. But once you are inside, the incredible works of Michelangelo, Botticelli, Carvaggio, and Titian should help reassure you that you have made a wise art history decision! After you’ve had the opportunity to immerse yourself and are ready for your next adventure, I’d recommend taking the time to explore the city on foot if you still have a solid portion of your day left. It is always a good idea to search out a gelato and then figure out what else you’d like to explore in the city. In terms of churches that are a worthwhile stop, the Duomo (the official name is Santa Maria del Fiore) and Santa Croce are two basilicas that are understandably on most people’s to-do lists when they visit Florence. If the weather is cooperating, then you might consider the Boboli Gardens, especially if you are there in the spring when all of the flowers are in bloom. There are many food markets throughout the city as well, so if your timing is right, you can acquire the necessary picnic ingredients while walking around in the morning, make your way to the gardens to enjoy your lunch and then take an hour or two to explore the gardens, admire the sculptures and take in the views of the city.

Siena is often associated with the Pallo, the horse race that is held twice a year around the famous Piazzo del Campo, on July 2nd and August 16th. As a result, the city is incredibly crowded during both of those times so unless the race is your main priority, it could be wise to find an alternative time to visit the city. The city itself is one of the most popular tourist destinations in all of the country so you certainly won’t be disappointed no matter when you decide to pay the city a visit. The Siena cathedral (also known as the Duomo) will likely be a highlight of your stay. If possible, I would recommend trying to hire a guide to take you around the city if you are interested in knowing more about the different churches, the history of the horse race, or other facts about the city. I’ve found that guidebooks and the internet can provide some basic information about cities, but having a local share the city’s history brings it to life in a way that can be quite captivating. I’ve only done a few guided city tours in my travels, but the one I did in Siena was among the best. In a city with as much history as Siena, there is an incredible amount you could learn, so instead of just strolling around and wondering about the historical significance of each building you pass, a guide can make the city come to life in just a few hours.

Pisa might be one of your bucket list places if you can’t envision a trip to Italy feeling complete without having the iconic photo of yourself where you appear to be pushing over the tower of Pisa. While you might not have realized that the Leaning Tower of Pisa was leaning from the time it was built in the 14th century, it is still an attraction that beckons to many travelers and is therefore very crowded. Plan ahead and you can avoid the lines and a long wait by buying your tickets online ahead of time so you have a timed entrance. Balance the crowds and the bustle with time to explore the medieval part of the city. You should meander through the Chiesa di Santa Maria della Spina and I’d also recommend a stroll along the Arno river to round out your trip to the city.

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Wine Tasting

If you enjoy wine, then you should make a point of visiting a number of vineyards while you are visiting the region. There are so many to choose from, it may sound silly, but it is tough to go wrong. I’d suggest trying out a mix of small, family-owned, vineyards and larger, more well-known vineyards, just to taste the various styles of wine that are produced here and so you can get different perspectives on wine making in this region. If possible, get recommendations once you are in the region from your hotel. If you choose to stay in an airbnb, the owners might have suggestions about places to go. Make sure that you try each of the different kinds of wine that are made in this region, including the famous Chianti Classico wine, distinguished by the label featuring a black rooster inside a pink circle.

When I took a bike tour in Tuscany several years ago, one of my guides took us to her family’s winery, NostraVita. NostraVita grows only certified organic sangiovese grapes and produces a limited number of bottles of wine every year, but I learned an incredible amount about wine making. We visited several wineries over the course of the week, but this was the only winery where I purchased wine and had it shipped it back to the United States - the wine was that outstanding. Because they only have Sangiovese grapes, they only produce four different wines, but each wine was incredible and, if you find yourself close to the town of Montalcino, this winery is well worth the detour.